


The 4 Times Winn Schott Tried to Confess, and the One Time Kara Did It First

by cranky_thesbian89



Category: Supergirl
Genre: BBQ, Cute Winn Schott Jr., F/M, Fluff, Game Night, Hurt Winn Schott Jr., Mon-El (Supergirl TV 2015) Being an Asshole, Some angst, Winnara, game out with this out of various ideas, haha lead, mon-el can die in a hole, or get stabbed by a pencil, winnara for life mofo
Language: English
Status: Completed
Published: 2020-08-19
Updated: 2021-02-09
Packaged: 2021-03-05 22:07:56
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 5
Words: 7,797
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25992646
Author URL: https://archiveofourown.org/users/cranky_thesbian89/pseuds/cranky_thesbian89
Summary: Winn Schott has always been Kara Danver’s best friend, her right hand man. But in his eyes she was always someone special to him. From the day they first met and he laid eyes on her, he knew he had fallen head over heels for her. And it didn’t help when she came out as a badass female superhero.“You look pretty without your glasses” he said as she walked out in the new Supergirl suit. He couldn’t help but say it outloud, it was the truth after all. She just brushed by it and ignored it, sure he wasn’t too fond of it but he decided to ignore it as well. After the next few days, weeks, months, days even, he had fallen deeper and deeper in love with Kara Danvers. And everytime he tried to confess he either chicken out or was cut short. But there was one time where Kara actually beat him to it
Relationships: Alex Danvers & Kara Danvers, Kara Danvers/Winn Schott Jr., Querl Dox/Nia Nal
Comments: 13
Kudos: 55





	1. The First Time: Game Night

The first time was during a game night. 

There was screaming going around the superhero's apartment. There was laughter and some cheering going on around the table. It was the superfriends annual game night and almost everyone was there this time. Kara had been getting up and down periodically getting herself and others drinks, or wanting to grab herself another potsticker. She walked back over to the table of her friends trying to play Monopoly.

“Hey you little ToyBoy! You landed on my property so you owe me money!” Nia said, getting angry at the nerdy boy for not paying up. 

“Hey! Don’t call me that!” he said, obviously getting super offended. Kara pulled the potsticker out of her mouth before taking her seat beside Winn. 

“Guys,guys. Please remember this is the game that can and will ruin friendships” she commented as she took the dice to do her turn. 

“It hasn’t happened to any of us yet and we play this every game night” Alex chimed in as she took a sip of her wine. She sat on a chair by herself, her legs were underneath her as she watched the game unfold in front of her. 

“There is actually an 89.673% chance that you will ruin your friendship Winslow. And it is increasingly higher with Nia since you haven’t known her for that long” Brainy said without looking up from the game board, he was planning out how the game might end. In his favor or not. 

“Thank you, Brainiac” Winn said with sarcasm laced in it. He grabbed the potsticker from the plate in front of Kara. He didn’t hesitate to take a bite before placing it back. He looked up and was met with the glaring face of Kara Danvers. His eyes widened as he put his hand in front of his mouth, trying to quickly eat the food in his mouth. 

“Did you just eat some of my potsticker?” she asked as she crossed her arms. 

“Uh…. No” he said as he gave her the most innocent smile he could muster up. Although it was hard to do with some food still in his mouth. 

“You have to stay behind and help clean” she simply stated as she moved her game piece. 

“But Karaaaaaa!” Winn whined, not really minding about staying behind but he did want to play some video games before he got some sleep. Well, he didn’t have to sleep but he knew Kara would get upset if he stayed up. The rest of the game night flew by and seemed to be pretty chill. There were various arguments over Brainy or Winn cheating in some capacity. Maybe even Kara cheating during charades. But the night soon came to an end around 10:15. Nia and Brainy were the first ones to leave, after all Nia had to finish an article for the next day. Not long after those two left, Alex said goodbye. Followed by James. It was finally just Winn and Kara left in her apartment, to clean up the small mess they had made. Kara stood at her kitchen counter, trying to wipe down various crumps and trash. Winn noticed and thought this would be the best time to try to sneak out of the apartment. He set down the trash bag he held in his hand, he was picking up the trash around the coffee table. He tried to sneak over to the door, glancing over to see if Kara was paying attention or not. His hand found its way onto the door handle, until he heard someone clear their throat.  
“Shit….” he muttered before turning to face Kara. He slightly waved as an awkward smile grew on his face.

“And where do you think you’re going Mr.Schott?” she asked, crossing her arms after she threw the towel over her shoulder. 

“Uh… no where” he said, awkwardly chuckling before he went back to the coffee table. Kara chuckled a bit as she walked over to where Winn now stood. 

“If this bores you, I can play music for you,” she said as she grabbed a paper plate and tossed it into the trash bag. Winn just shrugged as he continued to clean. She sighed as she went over to where she set her phone, deciding to play music to make the clean up session a little more fun. Soon, the beginning notes of Classic by MTKO played through her speakers. She smiled and started to hum as she grabbed the broom. She started to dance a little and pretended it was a microphone. Winn glanced over at her and couldn’t help but laugh. He was watching the most beautiful girl in the world, no, the universe, dance like nobody was watching. He crossed his arms and leaned against the couch, watching Kara perform a little. She smirked and walked up to Winn, offering her hand. “Come on nerd boy, dance with me” Winn scoffed and shook his head, pushing her hand away. 

“I don’t dan-” but before he could finish the sentence, Kara had her hand around his wrist, pulling him to her. 

“It wasn't a question Winn,” she said as he set down the trash bag. Soon enough they were dancing together and like the goofs they are. After the first song ended, the next song played, a nice smooth female voice singing You Matter to Me from the musical Waitress. But it was sung by Sara Bareilles instead of the cast of the musical. Since it was slower than the last one, he pulled Kara into his chest. One of his hands was laced with ers while the other was on the small of her back. They just swayed together, her hand on his chest. He couldn’t help but smile down at her, thinking this might be the best time. It had to be the time to admit his true feelings to the girl of his dreams. 

“Hey, hey Kara. Can we talk” he said, in the softest tone he could. 

“Hm?’ she hummed, taking her head off his chest and looking up to him. He chuckled softly, smiling down at her as he pushed a loose strand of hair behind her ear. 

“There’s been something I’ve been meaning to tell you. For a while actually and…” he was cut short by Kara looking at the window. 

“Hey...uh.. Winnn. I’m sorry. But I gotta go” she said as she stepped away. “You know, Supergirl stuff” she said, sending him a soft smile. Of course he understood but he hates that it had to happen now. He was so close. With that she took off, flying out the window. Her discarded clothes on a pile in front of Winn.


	2. Second Time: When Mon-el left

**Summary for the Chapter:**

> Kara is still in her depressed state after Mon-el left. Winn tried to help but also couldn't help but realise his love for her. Yet he cant say it yet.

**Notes for the Chapter:**

> This is a short one because there wasn't much I could think of writing. Although it's short I think it did the justice.

The second time was after Mon-el left 

It had only been a month since Kara had to send Mon-el into space to save him and she was still a mess. She would come into work but she would always put on a fake smile or she would force a laugh. Winn hated to see how heart broken Kara was over this. He tried his best to cheer her up anyway he could, surprising her with random donuts or ice cream. It brought a smile to her face but it never lasted. He wishes he could make her smile and laugh as much as Mon-el could. It was the usual Friday night and the friend group was wanting to go out to the alien bar for a few drinks after their day at the DEO. Everyone agreed to go, even Kara. But when the time came and everyone was around the table, Kara was nowhere to be seen. 

“Where is Kara?” Winn asked as he glanced around the bar, 

“MIA, like usual” Alex said with a sigh, taking a sip from her drink. 

“Hey, I’ll go check on her” Winn said, getting out of his chair and slipping on his black jacket. He said goodbye to everyone as he exited the bar, heading to Kara’s apartment. He got there about 15 minutes later, he stood in front of her door as he debated about actually knocking. He took a deep breath before bringing his hand to knock on the door. When he didn’t get an answer, he just brought his hand down to the knob and turned it. Of course, it was unlocked. He walked in, shutting and making sure to lock the door behind him. “Kara, why didn’t you come to the bar?” he asked, walking up to her where he assumed she was. He slid his jacket off, setting it on a nearby chair before turning to see the tear stained face of Kara, a tub of ice cream in hand. 

“I... I just couldn’t bring myself to show up” she said before shoving a spoonful of ice cream into her mouth. 

“You do realise your friends are here for you, right?” he said, sliding onto the couch beside her. “I am always here for you” 

“I know, I know but.. He isn’t here” she said, bringing her knees to her chest. Ah yes, of course the reason she couldn’t come out was because she had yet gotten over Mon-el. It makes sense how she hasn’t moved on but there were ways to help move on, going out with friends being one of them. Even just trying to talk to him or something would’ve helped. He just wanted to be there for her anyway he could be. But clearly she could never see it. 

“Kara, he’s gone and you’re gonna have to get past that. Someone else will come around and see how an amazingly beautiful person you truly are” he said, accidentally letting how he really feels about her out. 

“But who would want to date me? I’m an alien hot mess” she said, trying to bury her face into her knees, but it wasn’t going so well. Winn sighed to himself, scooting a bit closer to her. 

“Kara, look at me. Please” he said, gently placing a hand on her cheek. He used his thumb to wipe various tears away as he made her look at him. He looked her right in the eyes without saying anything. He just couldn’t bring himself to say anything. All he could think of is how in love with her he was, but he knew now would not be the best time to say anything. He sighed and brought her head to his chest. “You’ll find the perfect someone, just give it time” he said in a hush voice, running his fingers through her hair. Kara seemed to calm down at his touch, slowly falling asleep. When he noticed she’d practically passed out, a small smile grew onto his face as he kissed the top of her head.

**Notes for the Chapter:**

> I will keep posting as the chapters/part finish. I hope y'all are enjoying and don't hesitate to leave comments!


	3. The Third Time: at the BBQ

**Summary for the Chapter:**

> The one time Winn and Kara had some alone time and he almost admitted his feelings, but Eliza ruined it.

**Notes for the Chapter:**

> I am so sorry about the long wait but I had writers block in the middle of this. I will try to update as soon as I can. I also would like to say most of the star/space/nerdy facts are from my s/o who is basically the real life Winn Schott and I love em.

It had been a while since Kara and Clark had actually seen each other so they thought it would be nice to hold a little BBQ with both the Danvers and Kents. Sure, Kara brought along Winn, James, Nia, and Brainy but they counted as family at this point. Especially since James was friends with both Kara and Clark. They planned this a week before it even happened, yet when the day came everyone was beyond excited. They all agreed to meet up at Kara’s apartment so they could all drive to Clark’s farm. Kara had been up since 7, getting some snacks and drinks into a bag for the road trip. She also made sure to pack the chargers and books for herself. By the time 8:30 came around, only James and Alex had showed u p to her house. Kara was just about to say something when there was a knock on the door.

“Well, I’ll get that” James said, sending a smile to Kara. He was hoping it would calm her down, anyone could sense how stressed she was. As James opened the door, in walked Brainy and Nia. Nia carried a small picnic basket, a big smile on her face. 

“Sorry we’re late, I got carried away trying to finish these cookies and my mother's famous egg salad. We then stopped by the store to pick up some various food items” she explained as she sat the basket down,Brainy followed by putting down what seemed to be a bag of alcohol. 

“Oh please say that’s whisky” Alex said as she tried to rush over to it, but Kara’s arm stopped her.

“Now is not the time for that” she said before glancing between James and Brainy, “Any news on Winn?’ she asked, putting her hands in her pocket. 

“Well, I heard that he was running by a do-” Brainy started to say until Nia nudged him, giving him a look.

“He’s on his way now, don’t worry” she said as the look turned into a smile. Kara was confused and shrugged it off, 

“Well, let’s get packed up. I think two cars should be enough. I can drive car one and Alex can drive car two” Kara explained as she grabbed her bag.

“Then James and Winn will be riding with me” Alex said, plucking the whisky from the table and heading out the door. James chuckled and shook his head, smiling a bit. 

“I’ll make sure to keep on her, both of them actually” he said before following Alex. Kara and Nia looked at each other with a knowing look,

“Disney music the whole time?” Kara asked and Nia immediately nodded. They high fived before grabbing what they needed and heading down to the cars. When Alex got down to her car, Winn was just pulling up to his. He stepped out of his car before going to the drivers side, pulling you a bag and a box. Kara squealed a bit when she saw him. He couldn’t tell if it was because of him or what was in the box. He didn’t care as long as he gotta see her smile.

“Oh Winn, please tell me you got me some crullers” she said as she walked up to him. He didn’t even put his bag away before opening the box to show her, 

“You know I did,” he said, smiling at her.

“Oh I love you!” she said,l grabbing one before kissing his cheek and heading over to her car. Winn was frozen in shock, his cheeks turning a light shade of pink. James chuckled, putting a hand on Winn’s shoulder, 

“I see someone is slowly getting out of the friendzone,” he joked. Winn was just speechless, incoherent words came out of his mouth as he tried to process what was going on. This just made James laugh even more. Then, as if on cue there was a car honk. They both turned to see Alex, rolling a window down. 

“Get in losers, we’re going to a bbq” she said, putting some sunglasses on. Both boys laughed before getting in the car. James took the passenger seat while Winn sat in the back. Of course, he didn’t mind it, he could easily fall asleep if he got tired. 

“Hey Alex, did you hear what Winn did?” James asked, a small smirk on his face.

“Oh no no no, we don’t have to talk about that” Winn said, hoping they might just ignore it.

“No I did not, but do explain” she said, glancing back at Winn through her rearview mirror. 

“He brought your sister some donuts , which earned him a kiss on the cheek”

“Oh really?”

‘Yes but it doesn’t matter, it meant nothing” Winn said, trying to shrug it off. Alex gave him a look through the rearview mirror again. He said, annoyed with how well Alex could read him. “Alright fine…   
it meant something”

“Oh we know” James said before Alex joined in,

“All of us know about your feelings towards Kara, besides Kara herself. She is just too wrapped up in work and being Supergirl to realise anyone liking her” Winn was just quite the rest of the trip, a blush never leaving his cheeks. It took only three hours to get to the Kent farm, where they all agreed to have the bbq. When Alex, Winn, and James got out of their car Clark and Jereamiah were already at the grill, making various meat items. 

"Hi dad, hey Clark” Alex said, walking up to them and hugging them both. Winn helps bring various bags and items. 

“Aw thanks Winn, you’re such a sweetie” Eliza said, unpacking some food from the bags he brought in.

“Of course, anything for you Mrs,Danvers. Anything else I can help you with?” he asked, leaning against the counter a bit. 

“Oh no, I think I’ve got it under control from here but I will be sure to call for you if I need any help” she said before Winn left to go sit with James in the living room. They spent most of the time watching a movie while waiting for some food, soon enough everyone was called outside. There was a few tables with chairs,

“You guys serve yourselves and sit wherever” Clark said as he helped Lois set up a few things at the table. Winn went up, beyond excited to eat the cheeseburger. He grabbed a few before grabbing an empty chair, the chair beside him was soon filled by Kara. 

“Hey Winn”

“Oh hey Kara, how’s the bbq been so far?” he asked, striking up a conversation as he ate his burger. He hummed in content at the first bite, he knew Clark could cook but he didn;t think it would taste that good. Kara noticed and laughed a bit, 

“Is it that good?” she asked, taking a bite of her hot dog. 

“Oh it’s amazing!” he said before taking another bite from the burger. Kara justed watched in enjoyment as the boy beside her devoured his burger, she couldn't help but smile at his reaction. 

“So Kara, how’s your love life?” ELiza asked as she ate some potato salad. Kara just laughed, shaking her head before putting a strawberry into her mouth.

“My love life is basically nonexistent. I’ve been focusing on my work” 

“So there’s no one who peaks your interest?” her mom asks as she starts to eat some of the steak off her plate. Clearly she had someone in mind but she wasn’t wanting to say it. 

“No, Eliza, there isn’t anyone” Kara responded, being adamant that Eliza would listen to her. Eliza sighed a bit, sticking some steak in her mouth. Then, various conversations went around the table and   
Winn would jump in at certain moments. The dinner finally ended and everyone beside Winn and Kara went inside to play various board games. Winn had thought he was outside by himself, wanting the time to look up at the stars. But when he heard the sound of shoe’s against the pavement, he looked over. That’s when he saw Kara with her cardigan wrapped around her. 

“I’m assuming you’re out here for the stars too?” she asked, walking up to her. He chuckled, looking back up. 

“Of course I am. I am Agent Schott afterall, protector of the stars” Kara chuckled and tried not to lean against Winn, although she kinda wanted to. 

“So, what do you see?” she asked, trying to spark a conversation. 

“Well, do you see that right there?” he asked, pointing to a point at the sky. She squinted a bit, sighing when she couldn’t see it, “Come here” he said, gesturing for Kara to come to him. She nibbled on her bottom lip before she moved to stand in front of him. He was honestly shocked, he didn’t expect for Kara to actually move over to him. But he did put her arms around her slightly before lifting one arm up to the sky again. “Well, do you see that right there?” he asked. He could feel the small smile grow in her face, 

“Yeah, it’s a constellation. Right?” he asked, not moving from between Winn’s arms. 

“Yeah, it’s actually the Little Dipper, in Ursa Minor.”

“Oh yeah, I can see it,” she said, not moving from her spot. 

“If you follow the star at the tip of the handle…” His finger moved as he spoke. “You can find the Big Dipper, in Ursa Major. And between the two is Draco.”

“Malfoy?” Winn laughed.

“Well, it is what he’s named after.” he said. 

“Wait really?” she said, looking back at him. Although she had to look up a little bit, with Winn being just 2 inches taller than her. Winn laughed and shrugged, 

“I honestly don’t know but it’s a safe assumption. They got the name Beetlejuice from the Betelgeuse star” 

“God you're such a nerd” she said, chuckling while turning to face him. She forgot she was between his arms before they were nose to nose. They both felt their breathing hitch a bit but they didn’t move. Winn found himself glancing down at Kara’s lips. He wished he had the confidence to actually try to kiss her but instead he cleared her throat. 

“Yeah so...I have something to say,” he said, gaining enough confidence to admit something. Her eyebrow quirked a bit, he opened his mouth to say something till they heard the sliding door open. 

“Kara honey, could you please come in. Nia and James want smores and it’s too windy for a fire” Eliza said, getting Kara’s attention.

“Uh… I gotta go” she said in a hushed tone before snaking her way out of Winn’s arms and heading inside. Winn sighed, his eyes following her inside. When Kara got inside, she was soon asked questions from her mother. 

“What was happening out there sweetie?”

“I..uh.. I actually don’t know” she said, trying to ignore the blush on her cheeks. 

“Your blush tells a different story,” Alex said from her spot at the counter, taking a sip of wine after she spoke.

**Notes for the Chapter:**

> Don't hesitate to leave comments and make suggestions! I would also love suggestions for what I should write once this is done.


	4. The Fourth Time: Movie Night

**Summary for the Chapter:**

> Winn decides to try to attempt his feeling during one of their famous movie nights. The night was going great, until he actually tried to say something.

**Notes for the Chapter:**

> I am so sorry for how long it took for me to update the story. School has been a lot and very stressful. Plus I kinda went through some time of writers block. But I am back! (for now) and will update when I can. I will post the last and final chapter when I can. But it might be a little longer then past chapters, since it is the final. 
> 
> Thank you for you patience and comments. Hope you enjoy!

Movie Night was a huge thing for Winn and Kara. It was the night where it was just the two of them and hours of their favorite movies. Along with a mountain of all the best snacks. Some Kara even made herself, not too well though. It happened every other weekend and each time they took turns decided what genre, fandom, or movies to watch. This weekend was Winn’s turn and it was no shocker when he decided the original Star Wars trilogy. He had brought the movies to Kara’s house the day before the movie night was supposed to happen. He also brought some pillows and blankets then a bag with various items for the night. Throughout the day, Kara tried to focus on work but her mind kept wandering to Winn and their upcoming movie night. She was sitting at her desk, smiling to herself as her mind was wondering. She was brought out of the slight trance by someone tapping lightly on her desk. She looked up to see her sister, sparking confusion to why Alex would be here. 

“Uh, hey Alex” she said, sitting up straight and moving some hair out of her face. 

“I hate to be the bearer of bad news” Alex said, glancing around Catco a bit. Kara quirked an eyebrow a bit, even more confused. 

“What do you mean? What bad news?” 

“Well, Winn might be a little late to your movie night”

“What why? Is he okay?” she asked, quickly worrying about her friend. 

“Oh he’s fine. No need worry Kara” Alex said, sending her sister a small smile, “He just has some extra work he’s gotta do. Which means he will be at the DEO a bit later than planned.” Kara let out a breath she didn’t even realize she held. Of course she would worry about her friend, since Winn was her best friend. He was friends with her ever since she came to Catco. She’s worried about him countless times but she never worried about him over such a small thing. She shrugged it off, trying not to think too much of it. 

“Well, tell him I will start A New Hope whether he is on time or not” she said, a small laugh escaping her lips. “And I may eat all the popcorn” she said as she felt her phone start to vibrate. She gave her sister a small smile before looking at her phone, “I gotta go. An interview of mine has been confirmed and it’s soon” she said, getting out of her chair while getting her pink jacket off the back of her chair. 

“Well, I’ll let you get to it.” she said, giving Kara a small hug, “But you owe me a lunch another day. With details of everything that happens tonight” Alex said, smoking a bit. She gave Kara a wink before she started to leave, 

“Hey! Nothing will happen tonight!” she said, trying to ignore the blush finding its way to her cheeks. Even though she got no reaction from Alex, she knew that she’d be laughing. Kara let out a sigh before she went off to her interview. The interview took longer than she had hoped but she still made it to her apartment in time to start the popcorn and get the movie night ready. She immediately threw her coat onto a chair when she walked into the door. “Okay so popcorn, cookies, wine, ice cream, and pizza has to be made and ordered” she said, marching right over to the kitchen. She decided to start by making the cookie dough, since those would take the longest to bake. After a while, the cookies were in the oven and about ¼ of the wine bottle was gone. She dusted her hands off on her pants before picking up the phone, “Hi yes, I’d like to order some pizza” she said, placing her hand on her waist. “Uh… two large pizzas. One meat lover and one just pepperoni with extra cheese” she glanced around the room, walking up to the fridge to see what was all in there, “Oh! And an order of cheesy bread” she said, seeing that they might need more snacks. “Names Kara” she said before telling the guy her address. The minute she got off the phone, she went to her room. Deciding that being in pajamas would be better then her work clothes. She heard the timer ding before she could get her light blue cardigan on. She grabbed it and rushed to pull the cookie out of the oven. She smiled to herself, proud that she didn’t burn them. This time. “Ooooh yes! They aren’t burnt!” she said proudly, setting them out so they could cool. She got out another wine glass, filling them both up before putting a bag of popcorn in the microwave. Followed by another one when it was done. She filled a big bowl with the popcorn, coating it with butter. 

“The more butter the better” Winn would always say. A fond smile grew on her face as she remembered all the past movie nights she’s had with the genius boy. All the movies, slight cuddles and longing glances. The tired flirting Winn had attempted to do multiple times that would lead to her having some sleepless night. ‘Did he actually mean what he said? Was it the alcohol? Him not getting enough sleep?’ she’d always think but to keep going, she’d push the thoughts to the back of her head. She had just finished setting up the living room, There were a few blankets and pillows on the couch; the popcorn, wine and cookies sat on the coffee table. She took another sip of the wine as she heard the knock on the door. Assuming it was the pizza, she passed A New Hope, right as Luke met Obi-Wan. “I’m coming!” she said, setting the wine down and then going to open the door. She opened the door to see Winn standing there, the pizza boxes in his hand. “Well, the pizza guy looks different” Kara jokes, stepping aside to let Winn come in. 

“Hey, it’s my side gig. Don’t judge” he responded, setting down the pizza and his side bag on her small island. “I saw the pizza guy in the way up, decided to pay and bring it to you”

“Well, how much do I owe you?”

“Uh, a glass of wine and do I smell fresh baked cookies?” he asked, heading over to the coffee table, a smile growing on his face. 

“Yeah but don’t complain if they aren’t good! I made them from scratch” Kara said, opening the box of pizza to grab herself a slice. 

“They’re from you so I bet they’ll be delicious” he said, picking one up and taking a huge bite. He coughed a bit as he slowly said, “Deliciously sweet!” he said, sending Kara a fake and slightly pitiful smile. 

“Oh shut up! You don’t have a healthy diet so you don’t try me” she said, taking a bit of her pizza. He laughed, shrugging a bit before taking another bite of the cookie. Soon they both sat on the couch, pizza now in front of them as well. Kara brought her legs up underneath her before Winn scooted closer, throwing a blanket over the both of them. She felt a blush spread across her face, not expecting Winn to want to be this close to her. It wasn’t unusual but after what happened at Clark’s a few weeks ago, she thought some stuff was different about them. Clearly she was wrong. 

“You alright Kara?” Winn asked, earning Kara to look over at him. 

“Oh yeah, I’m fine” she said, nodding a bit. “Just excited to start the movie! Even though I started it a bit earlier” she said, shrugging a bit.

“I know, Alex warned me,” he said, sending her a joking glare. 

“I’m sorry I didn’t wanna wait” she said before grabbing the remote and playing the movie. 

“Oh yes! I didn’t miss them introducing Han!’ Winn muttered while grabbing a slice of pizza. Kara let out a small chuckle before taking a sip of wine and putting her focus back on the movie. About an hour later, they both were snuggled up to each other. Most of the pizza was gone, they were on their 3rd bottle of wine, only 4 cookies were left and there was no more popcorn or ice cream. “Are you done with all of these?” Kara asked, standing up to clean up a bit. 

“Yeah, just keep the cookies” he said, reaching forward to grab another cookie. She laughed as she picked up the pizza boxes, 

“At least someone enjoys my baking” she joked, taking the trash over to the trash can. 

“Should I pause the movie?” he asked, turning a bit to look at her from the couch.

“Since we’ve watched it so many times, I think I’ll be good,” she said, grabbing the trash bag and towards her door. “I’ll be back,” she said, walking out. Winn watched her leave, letting out a small sigh as the door shut. 

“Come on Winslow, you can tell your best friend how much you love her. You kissed her once before but it doesn’t mean you can’t try again” he rambled to himself quietly, trying to gain the confidence he needs. He quickly stopped talking as Kara came back, hoping she heard none of his small conversation with himself. 

“Back to the movie!” she said, rushing over and snuggling back up to Winn’s side. Although she didn’t even realise she had done it. A small blush came onto Winn’s face, deciding to slowly wrap an arm around her shoulder. ‘If she asks, it’s to be a little more comfy’ he told himself to say if she would question. Thankfully she didn’t though, and they just went on with the movie night. They had finally gotten to The Empire Strikes Back, over the past few hours Kara decided to lay down. She had put her head on Winn’s lap so she could still watch the movie, at the same time he was running his fingers through her hair. The Han and Leia ‘I love you’ scene was about to happen and he thought maybe he should tell her around then, since it was so on point. He took a deep breath before deciding to speak up, 

“Hey Kara?” he asked looking down at her. An eyebrow quirked when he didn’t get a response, “Kara?” he asked again,shaking her a bit. A sigh escaped his lips when he realised she had fallen asleep on his lap. Of course, he wasn’t against it but it messed with what he had planned to do. “Well, I’ll say it even if you can’t hear it. “ he said, deciding to just say it anyways. Better to get it off his chest. “Kara Danvers, you are my best friend but I see you as even more. I know you might not see me the same way but one day I hope that you love me as much as I love you. Which is honestly a lot.I honestly fell for you the moment you walked into Catco that first time. Sure you were stressed but you just seemed perfect to me. Then you became my closest friend, I kept falling for you more and more each day. Then you decided to come out as Supergril. Well, you have honestly been my hero since the very beginning. And now I’m just rambling about how much I love you since you are asleep and hopefully can’t hear any of this” he said, rambling out in one breath. Once he finished, he took in a big breath before letting it out. He was honestly very happy he had done that, it did take a load off his shoulder. With that, he decided to try to get some sleep himself. Although he would do it on the couch, not wanting to disturb Kara’s slumber.

**Notes for the Chapter:**

> Don't hesitate to leave comments and make suggestions! I would also love suggestions for what I should write once this is done.


	5. The Realization

**Summary for the Chapter:**

> Something happens to Winn that makes Kara realizing the truth that she had been burying this whole time.   
> While Winn his living his dream life, Kara is living a nightmare as she tries to save the love of her life.

**Notes for the Chapter:**

> Once again, I am so sorry for the late update but I am happy to say this is an end to a story I have loved writing. I hope you all enjoyed reading it as well. I will let you know that I will be writing a lot more and for other fandoms. And I just made a Winnara oneshot book (go and check it out man), and be sure to comment any ideas you'd like to see be fleshed out there. Thank you for all the comments and for supporting this story. I'll be sure to update my other stories later.

It was a big fight, no surprise to anyone. As Kara and Nia were trying to stop the new rising threat, The Daydreamer, he was trying to attack anyone he could. He was an alien that could put anyone in a daydream like trance and gain energy off their hopes and dreams. The Daydreamer had knocked Kara aside as he laid his eyes on a certain light brown haired boy.  
“Oh, no no no” he muttered as he stumbled out of his chair, trying to escape from the alien. “Shit...” he muttered again, realizing there was no escape. He was soon pinned to the ground as a hand covered his eyes. Soon all her saw was black. It didn’t take long for him to be woken by something. Wait, no someone.   
“Come on Winnie bear, you gotta get up or we can’t start that Marvel marathon the kids and you planned” he heard an all too familiar voice say. Kids? He thought, being very confused. What he saw when he opened his eyes confused him even more. There on top of him, well slightly on top of him, was Kara. Although she did look slightly older, but still good for her age. He blinked a bit while slowly sitting up,   
“Uh… morning” he said as he looked around the room, trying to take everything in. He took in the light walls with framed pictures and some certificates that seemed to have Kara’s name. But there was something specific that caught his attention, on the wall above a desk was Kara’s Supergirl suit but it seemed to be framed. Had she given up being Supergirl for him? Wait did she say they had kids? Maybe it was for the kids? His mind went on a whole rambling moment until.   
“You better hurry honey, don’t want the kids to burn down the kitchen” Kara said from her new spot at the door. She let out a small chuckle as Winn finally laid eyes on her frame. She still seemed to be the Kara he had originally fallen for. He let out a sigh as a small smile formed on his face. But he quickly shook his head as he came back to reality. This is NOT real. Him and Kara aren’t married and nor do they have kids. He wants to know what is going on but he has no way to figure out. He decided the best thing to do would be to just go with it. He slowly got out of bed, thankful he actually had pants on. He didn’t want to deal with the embarrassment of Kara seeing… you know what.  
“I’ll be right out, don’t wait up” he said, giving Kara a small smile before he headed for the door himself. He soon walked down a hall and into a kitchen area that led right into a living room. There were two kids in the kitchen, a boy and girl. The girl seemed to be older, having long blonde hair and blue eyes, there was no doubt that she was Kara’s kid. And then the little boy, in Star Wars pajamas and hazel eyes but with blonde hair. Definitely his kid as well. He felt a tingly feeling inside as if this was the world and it’s just what he wanted. A happy life with Kara, his Kara, and two beautiful kids. 

Meanwhile, at the DEO, Kara was pacing outside of the medbay. She had gotten The Daydreamer captured and he was put away but now Kara was beyond worried about her friend. He was still unconscious but his brain activity was perfectly fine. It's like if he was just normally asleep or something but he wasn’t, since the daydreamer did something. She stopped pacing, mentally preparing herself and taking a deep breath before walking into the medbay.  
“So, Alex, how is he?” she asked, crossing her arms. She might be talking to Alex but her main focus was on Winn as he just laid there, helpless. She wanted to find a way to help him, she would do anything.   
“Well he seems to be dreaming of something. And it’s something good” Alex said as she watched his brain activity. She then turned to Kara, giving her a soft smile. “Hey, he’ll be fine. We will find a way to wake him up but we can’t do it if you’re stressed. Go home and take a break” she said, which earned her a look of disapprovement from Kara.   
“I’m not leaving until I know Winn is awake and okay” Kara refused to go home for various reasons. Some of which she didn’t realize or want to admit yet.   
“Winn would hate to wake up and see you like this. He’d want you to go home” Kara pursed her lips as she contemplating before sighing in defeat,   
“Fine, just tell me when even the slightest thing happens” she said before walking out of the medbay. She walked up to the entrance before taking off and flying home. 

Back in Winn’s little dream, he sat on the couch with a kid on either side of him as he had a plate of messy scrambled eggs, some microwaved sausage, and what seemed to be pancakes with various candies on top.   
“I hope you like it dad! Jeremiah kinda went crazy on the candy” the blonde girl said as he noticed Kara leaning against the door from in the corner of his eye. She crossed her arms and watched him with the kids, a small smile on her face. And the way she looked at him, oh it could just melt it away.  
“I did not! Just cause you’re named after Princess Leia doesn’t mean you are always right!” the little boy, who he found out to be named Jeremiah, said. Of course, one kid has a Star Wars reference as a name while the other is special to Kara.   
“Hey, hey. I’m sure I’ll love it after all” he said, looking between Jeremiah and Leia.   
“After all, your dad does have a sweet tooth” Kara chimed in from her place at the door.   
“Well of course I do, look who I married” he said before even thinking. What was he doing? This wasn’t real, yet it felt so real to him.   
“You married the women you love”   
“And I hope you married me because you love me too”  
“Well of course I do” she said, walking up to him. She bent down and placed a small yet gentle kiss on his lips.

“Kara, come back now. Winn moved in his sleep and I don’t know man” Kara heard Alex on the phone. She had been at her apartment for about half an hour and already changed out of her super suit and into a pair of black leggings and a flannel that she doesn’t remember owning.   
“I’ll fly right over” she said before hanging up and quickly flew out the window. She arrived at the DEO, still in her lounge clothes, and rushed to the medbay. But when she arrived, she saw Alex pinned against the wall by none other than The Dreamer. “What the...I thought we captured you!”   
“Well, you did. But you are taking a tad bit too long to learn my lesson” he said, earning a groan from Alex.   
“Oh not the lesson crap again.” Alex commented.  
“But I have already learned a lesson, The Music Meister made me do it”  
“Oh well you see. Him and I had a…” The Dreamer cracked his neck a bit before letting Alex fall to the floor, “little disagreement. He wanted you to learn your lesson about your last guy while I want you to learn your lesson with….” he said as his gaze panned over to Winn. Kara looked at Winn as well before looking back at The Dreamer.  
“A lesson with Winn? What lesson would there be with Winn?” she asked, being ultimately confused. The Dreamer snicked, walking up to Kara.   
“Wow, you really don’t pay attention do you? The way he looks at you, how helpful he is with you. Not to mention the blatant flirting”  
“I have no clue what you mean” Kara said, crossing her arms as she denied everything.   
“But I do! “ Alex said.  
“Everyone does. Besides you” he spoke, pointing at Winn, “And him”Kara just gave him a confused look before she felt lightheaded. Suddenly she saw the movie night she had with Winn, but from a third person point of view.  
“What? What’s going on?” she asked as she looked around her own apartment.   
“Hey Kara?” she heard Winn say from beside her, seeing him shake her a bit. He was trying to wake her up.“Kara?” he shook her again. He let out a small sigh and she quirked an eyebrow. Being confused by what is going on. “Well, I’ll say it even if you can’t hear it.” she heard him say, now being even more confused.“Kara Danvers, you are my best friend but I see you as even more. I know you might not see me the same way but one day I hope that you love me as much as I love you. Which is honestly a lot.I honestly fell for you the moment you walked into Catco that first time. Sure you were stressed but you just seemed perfect to me. Then you became my closest friend, I kept falling for you more and more each day. Then you decided to come out as Supergril. Well, you have honestly been my hero since the very beginning. And now I’m just rambling about how much I love you since you are asleep and hopefully can’t hear any of this” She felt her breath get caught in her throat. He likes her? He still likes her, even after the first time she rejected him. That time she made a mistake.   
“I love you too…” she found herself subconsciously saying. Just as fast that she saw her apartment appear, it left. Now there was a Winn sitting up on the medbay table and Alex right at his side. She stumbled a bit, catching Alex’s attention.   
“Kara! Are you okay?” she asked, running up to her sister.   
“The Dreamer? Where… where is he?” she asked, looking around before her eyes landed on Winn. “Winn’s awake” she said, a smile growing on her face the same time a blush grew on her face.  
“Yeah. Here, let me help you up and you can see him” Alex helped her up and over to the bed. There she sat on a chair nearby, offering Winn a small smile.   
“I’ll leave you two alone” and With that, Alex walked out of the medbay, shutting the door behind her.   
“Hey, are you okay?” Kara asked, placing a hand on top of his.   
“Yeah, just kinda light headed and confused.”  
“Well what happened?”   
“He sent me into this type of dream wealm or something”  
“Or something?”  
“Yeah, like an alternate reality”  
“Well, were you Tony Stark there?” she joked, wanting to see him smile or even laugh. He did let out a small chuckle,   
“No, something completely different after all. It kinda involved you” Kara let out a shocked bit of breath, the blush on her cheeks seemingly getting darker.   
“Wait really?”   
“Um…. yeah. I don’t think you’d really be interested in the other details” he said, glancing away. But he soon felt a soft, reassuring squeeze on her his,   
“No, come on. I’m curious”  
“Well…” he cleared his throat a bit before he continued to talk. “It was based in the future and we seemed to be married with two kids.”  
“Married?” she asked, he just nodded,   
“Mhm, with two kids. A little girl named Leia and a boy named Jeremiah. Who tried to make me breakfast. Key word try” he said, earning a laugh from Kara.   
“Go on” she said, nodding her head a bit. And that’s what he did. But it didn’t take him too long to be cut off by a pair of soft lips on his. Something he’s been wanting for long. When they pulled away, they rested against each other's forehead as they just stared into each other's eyes.  
“I love you…” Kara muttered with a small smile on her face.   
“I love you too…” Winn muttered back, a smile on his face as well. She should’ve realized how much he’s meant before and that she did love him. She just always pushed it to the back of her mind, not wanting to ruin such a good friendship. But she can now say that she didn’t ruin the relationship, she made it better and into a relationship. She knew she would be happy more often.

**Notes for the Chapter:**

> Oh and please do check out my etsy! The only thing I am doing right now may be something that interests you. You can get an letter from a fictional character of your choosing! And if you don't have the money for that, I do have a different option. So just check out the link below.
> 
> https://linktr.ee/WriteWhatYouKnow

**Author's Note:**

> Don't hesitate to leave comments with suggestions or critic me. I write for a lot more fandoms so don't hesitate to ask.


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